#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/44/2224456.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224456
loop_
_publ_author_name
'Malik, Khizar Iqbal'
'Munawar, Munawar Ali'
'Khan, Misbahul Ain'
'Nadeem, Sohail'
Mukhtar-ul-Hassan
_publ_section_title
(4Z)-4-[(2E)-1-Hydroxy-3-(4-methoxyphenyl)prop-2-enylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one
_journal_coeditor_code           SU2151
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3046
_journal_paper_doi               10.1107/S1600536809046200
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H18 N2 O3'
_chemical_formula_moiety         'C20 H18 N2 O3'
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36
_chemical_name_systematic
;
(4Z)-4-[(2E)-1-Hydroxy-3-(4-methoxyphenyl)prop-2-enylidene]-3-
methyl-1-phenyl-1H-pyrazol-5(4H)-one
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.626(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0803(2)
_cell_length_b                   22.7645(9)
_cell_length_c                   14.5880(6)
_cell_measurement_reflns_used    3228
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.75
_cell_measurement_theta_min      2.28
_cell_volume                     1672.19(12)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9137
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.28
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2056
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0492P)²+0.0958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                2628
_reflns_number_total             2056
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2151.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2224456
_cod_database_fobs_code          2224456
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 x,-y,1/2+z
3 1/2+x,1/2+y,z
4 1/2+x,1/2-y,1/2+z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 -0.0176(4) 0.44681(8) 0.51341(14) 0.0664(7) Uani . . 1.000
O O2 0.3841(4) 0.46097(8) 0.63360(16) 0.0711(7) Uani . . 1.000
O O3 1.6238(3) 0.37711(9) 1.04514(13) 0.0698(7) Uani . . 1.000
N N1 -0.1696(3) 0.34974(9) 0.51051(14) 0.0509(7) Uani . . 1.000
N N2 -0.0989(4) 0.29740(9) 0.55796(15) 0.0553(7) Uani . . 1.000
C C1 1.0015(4) 0.41049(11) 0.83769(17) 0.0485(7) Uani . . 1.000
C C2 1.0508(5) 0.35476(12) 0.8761(2) 0.0582(9) Uani . . 1.000
C C3 1.2597(5) 0.34518(11) 0.9444(2) 0.0596(9) Uani . . 1.000
C C4 1.4271(4) 0.39123(12) 0.97629(17) 0.0525(8) Uani . . 1.000
C C5 1.3838(4) 0.44665(10) 0.93893(17) 0.0493(8) Uani . . 1.000
C C6 1.1739(4) 0.45543(11) 0.87062(17) 0.0503(8) Uani . . 1.000
C C7 0.7813(4) 0.42297(12) 0.76621(17) 0.0509(8) Uani . . 1.000
C C8 0.5954(4) 0.38652(12) 0.72645(17) 0.0520(8) Uani . . 1.000
C C9 0.3848(4) 0.40523(12) 0.65663(17) 0.0520(8) Uani . . 1.000
C C10 0.1866(4) 0.36961(11) 0.61184(16) 0.0476(7) Uani . . 1.000
C C11 0.1116(4) 0.30908(11) 0.61679(17) 0.0499(8) Uani . . 1.000
C C12 -0.0042(4) 0.39408(11) 0.54131(16) 0.0508(8) Uani . . 1.000
C C13 -0.3813(4) 0.34899(10) 0.43652(17) 0.0495(8) Uani . . 1.000
C C14 -0.5624(5) 0.30347(11) 0.43192(19) 0.0546(8) Uani . . 1.000
C C15 -0.7691(5) 0.30167(13) 0.3600(2) 0.0689(10) Uani . . 1.000
C C16 -0.7933(6) 0.34472(14) 0.2929(2) 0.0789(11) Uani . . 1.000
C C17 -0.6134(6) 0.38955(15) 0.2983(2) 0.0745(11) Uani . . 1.000
C C18 -0.4058(5) 0.39282(13) 0.3700(2) 0.0646(10) Uani . . 1.000
C C19 1.8035(5) 0.42227(14) 1.0791(2) 0.0716(10) Uani . . 1.000
C C20 0.2392(5) 0.26103(12) 0.6752(2) 0.0690(10) Uani . . 1.000
H H2 0.94040 0.32360 0.85510 0.0700 Uiso calc R 1.000
H H2O 0.25380 0.46790 0.59560 0.1070 Uiso calc R 1.000
H H3 1.28940 0.30780 0.96930 0.0720 Uiso calc R 1.000
H H5 1.49530 0.47760 0.95970 0.0590 Uiso calc R 1.000
H H6 1.14600 0.49280 0.84550 0.0600 Uiso calc R 1.000
H H7 0.76850 0.46160 0.74540 0.0610 Uiso calc R 1.000
H H8 0.60180 0.34730 0.74450 0.0620 Uiso calc R 1.000
H H14 -0.54550 0.27420 0.47690 0.0650 Uiso calc R 1.000
H H15 -0.89240 0.27130 0.35690 0.0830 Uiso calc R 1.000
H H16 -0.93130 0.34320 0.24420 0.0950 Uiso calc R 1.000
H H17 -0.63050 0.41850 0.25290 0.0890 Uiso calc R 1.000
H H18 -0.28550 0.42380 0.37350 0.0770 Uiso calc R 1.000
H H19A 1.87980 0.43950 1.02860 0.1080 Uiso calc R 1.000
H H19B 1.94210 0.40600 1.12290 0.1080 Uiso calc R 1.000
H H19C 1.71030 0.45190 1.10880 0.1080 Uiso calc R 1.000
H H20A 0.14180 0.22520 0.66150 0.1040 Uiso calc R 1.000
H H20B 0.23990 0.27080 0.73920 0.1040 Uiso calc R 1.000
H H20C 0.41850 0.25590 0.66260 0.1040 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O3 C19 . . . 117.6(2) no
C9 O2 H2O . . . 109.00 no
N2 N1 C12 . . . 111.33(18) no
N2 N1 C13 . . . 118.97(19) no
C12 N1 C13 . . . 129.6(2) no
N1 N2 C11 . . . 106.58(19) no
C2 C1 C6 . . . 117.3(2) no
C6 C1 C7 . . . 119.6(2) no
C2 C1 C7 . . . 123.1(2) no
C1 C2 C3 . . . 121.1(2) no
C2 C3 C4 . . . 120.2(2) no
O3 C4 C3 . . . 115.2(2) no
O3 C4 C5 . . . 124.9(2) no
C3 C4 C5 . . . 119.9(2) no
C4 C5 C6 . . . 119.1(2) no
C1 C6 C5 . . . 122.4(2) no
C1 C7 C8 . . . 128.7(2) no
C7 C8 C9 . . . 122.8(2) no
O2 C9 C8 . . . 116.3(2) no
O2 C9 C10 . . . 117.9(2) no
C8 C9 C10 . . . 125.8(2) no
C9 C10 C11 . . . 136.0(2) no
C9 C10 C12 . . . 119.5(2) no
C11 C10 C12 . . . 104.56(19) no
N2 C11 C20 . . . 119.0(2) no
C10 C11 C20 . . . 129.7(2) no
N2 C11 C10 . . . 111.2(2) no
O1 C12 N1 . . . 126.6(2) no
N1 C12 C10 . . . 106.3(2) no
O1 C12 C10 . . . 127.1(2) no
N1 C13 C14 . . . 118.6(2) no
C14 C13 C18 . . . 120.6(2) no
N1 C13 C18 . . . 120.8(2) no
C13 C14 C15 . . . 119.5(2) no
C14 C15 C16 . . . 120.3(3) no
C15 C16 C17 . . . 119.6(3) no
C16 C17 C18 . . . 121.4(3) no
C13 C18 C17 . . . 118.6(3) no
C1 C2 H2 . . . 119.00 no
C3 C2 H2 . . . 119.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C4 C5 H5 . . . 120.00 no
C6 C5 H5 . . . 120.00 no
C1 C6 H6 . . . 119.00 no
C5 C6 H6 . . . 119.00 no
C1 C7 H7 . . . 116.00 no
C8 C7 H7 . . . 116.00 no
C7 C8 H8 . . . 119.00 no
C9 C8 H8 . . . 119.00 no
C13 C14 H14 . . . 120.00 no
C15 C14 H14 . . . 120.00 no
C14 C15 H15 . . . 120.00 no
C16 C15 H15 . . . 120.00 no
C15 C16 H16 . . . 120.00 no
C17 C16 H16 . . . 120.00 no
C16 C17 H17 . . . 119.00 no
C18 C17 H17 . . . 119.00 no
C13 C18 H18 . . . 121.00 no
C17 C18 H18 . . . 121.00 no
O3 C19 H19A . . . 110.00 no
O3 C19 H19B . . . 109.00 no
O3 C19 H19C . . . 109.00 no
H19A C19 H19B . . . 109.00 no
H19A C19 H19C . . . 109.00 no
H19B C19 H19C . . . 109.00 no
C11 C20 H20A . . . 109.00 no
C11 C20 H20B . . . 109.00 no
C11 C20 H20C . . . 109.00 no
H20A C20 H20B . . . 110.00 no
H20A C20 H20C . . . 109.00 no
H20B C20 H20C . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C12 . . 1.266(3) no
O2 C9 . . 1.313(3) no
O3 C4 . . 1.358(3) no
O3 C19 . . 1.420(3) no
O2 H2O . . 0.8200 no
N1 N2 . . 1.401(3) no
N1 C13 . . 1.419(3) no
N1 C12 . . 1.352(3) no
N2 C11 . . 1.307(3) no
C1 C2 . . 1.396(4) no
C1 C7 . . 1.453(3) no
C1 C6 . . 1.390(3) no
C2 C3 . . 1.373(4) no
C3 C4 . . 1.391(4) no
C4 C5 . . 1.380(4) no
C5 C6 . . 1.374(3) no
C7 C8 . . 1.331(3) no
C8 C9 . . 1.440(3) no
C9 C10 . . 1.387(3) no
C10 C11 . . 1.434(3) no
C10 C12 . . 1.430(3) no
C11 C20 . . 1.482(4) no
C13 C18 . . 1.386(4) no
C13 C14 . . 1.381(3) no
C14 C15 . . 1.383(4) no
C15 C16 . . 1.379(4) no
C16 C17 . . 1.365(5) no
C17 C18 . . 1.385(4) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C5 H5 . . 0.9300 no
C6 H6 . . 0.9300 no
C7 H7 . . 0.9300 no
C8 H8 . . 0.9300 no
C14 H14 . . 0.9300 no
C15 H15 . . 0.9300 no
C16 H16 . . 0.9300 no
C17 H17 . . 0.9300 no
C18 H18 . . 0.9300 no
C19 H19A . . 0.9600 no
C19 H19B . . 0.9600 no
C19 H19C . . 0.9600 no
C20 H20A . . 0.9600 no
C20 H20B . . 0.9600 no
C20 H20C . . 0.9600 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2O O1 . 0.82 1.77 2.529(3) 153 yes
C7 H7 O2 . 0.93 2.37 2.743(3) 104 no
C14 H14 N2 . 0.93 2.47 2.792(3) 100 no
C18 H18 O1 . 0.93 2.36 2.947(3) 121 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C19 O3 C4 C3 . . . . 178.9(2) no
C19 O3 C4 C5 . . . . -2.2(3) no
C12 N1 N2 C11 . . . . -1.0(3) no
C13 N1 N2 C11 . . . . 175.09(19) no
N2 N1 C12 C10 . . . . 0.6(2) no
C13 N1 C12 C10 . . . . -174.9(2) no
N2 N1 C13 C14 . . . . 20.3(3) no
C12 N1 C13 C14 . . . . -164.5(2) no
N2 N1 C13 C18 . . . . -159.5(2) no
C12 N1 C13 C18 . . . . 15.8(4) no
N2 N1 C12 O1 . . . . -178.9(2) no
C13 N1 C12 O1 . . . . 5.5(4) no
N1 N2 C11 C20 . . . . -177.8(2) no
N1 N2 C11 C10 . . . . 0.9(3) no
C7 C1 C2 C3 . . . . -179.2(2) no
C2 C1 C6 C5 . . . . -0.8(4) no
C6 C1 C2 C3 . . . . 0.7(4) no
C6 C1 C7 C8 . . . . -179.5(2) no
C2 C1 C7 C8 . . . . 0.4(4) no
C7 C1 C6 C5 . . . . 179.2(2) no
C1 C2 C3 C4 . . . . -0.2(4) no
C2 C3 C4 C5 . . . . -0.3(4) no
C2 C3 C4 O3 . . . . 178.7(2) no
O3 C4 C5 C6 . . . . -178.7(2) no
C3 C4 C5 C6 . . . . 0.2(3) no
C4 C5 C6 C1 . . . . 0.3(4) no
C1 C7 C8 C9 . . . . 179.2(2) no
C7 C8 C9 C10 . . . . 179.4(2) no
C7 C8 C9 O2 . . . . -0.1(4) no
O2 C9 C10 C11 . . . . -178.3(3) no
C8 C9 C10 C12 . . . . -177.7(2) no
O2 C9 C10 C12 . . . . 1.8(3) no
C8 C9 C10 C11 . . . . 2.3(4) no
C12 C10 C11 C20 . . . . 178.0(2) no
C9 C10 C12 O1 . . . . -0.5(4) no
C9 C10 C12 N1 . . . . 179.9(2) no
C11 C10 C12 O1 . . . . 179.5(2) no
C11 C10 C12 N1 . . . . -0.1(2) no
C9 C10 C11 N2 . . . . 179.5(3) no
C9 C10 C11 C20 . . . . -2.0(5) no
C12 C10 C11 N2 . . . . -0.5(3) no
N1 C13 C14 C15 . . . . -179.5(2) no
C18 C13 C14 C15 . . . . 0.2(4) no
N1 C13 C18 C17 . . . . 178.9(2) no
C14 C13 C18 C17 . . . . -0.8(4) no
C13 C14 C15 C16 . . . . 0.5(4) no
C14 C15 C16 C17 . . . . -0.7(4) no
C15 C16 C17 C18 . . . . 0.0(5) no
C16 C17 C18 C13 . . . . 0.7(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743781
